Sodium hydride → HCID 86757267, compound

HRID 651327Notes

Reaction equation

[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([CH3:41])[C:31]1=[O:42]>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[CH:7]([N:8]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([CH3:41])[C:31]1=[O:42])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-(diphenylmethylene)glycine t-butyl ester (1.30 g, 4.40 mmol) in 10 mL of DMF is treated with sodium hydride (60% in mineral oil, 0.250 g, 6.25 mmol) at 25° to give a red orange solution. After 1 h, the temperature is raised to 60° C. and a solution of the title B compound, 3-(4-iodobutyl)-1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinazoline (1.58 g, 4.41 mmol) in 10 mL of DMF is added dropwise over 10 min. After stirring for 5 h at 60° C. and 58 h at 25° C. the solvent is evaporated under reduced pressure, and the residue is partioned between 75 mL of ethyl acetate and 25 mL of water. The organic solution is washed with three 25 mL portions of brine, dried over anhydrous MgSO4, and concentrated to give 2.15 g of 2-(benzhydrylideneamino)-6-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinazolin-3-yl)hexanoic acid t-butyl ester as a yellow oil.

Workup

customto give a red orange solution
customis evaporated under reduced pressure
washThe organic solution is washed with three 25 mL portions of brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-ab264d49398e480bae2c9d288e0fa6a7
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277987B1

Reaction notes

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